A wooden mill with a water wheel, surrounded by autumn foliage and a calm river.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Waynesboro condo rentals

A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
$168 nightly
The price is $189
Sep 29 - Sep 30
Total with taxes and fees
Where the Trail Ends
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

2. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (129 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$221 nightly
The price is $248
Sep 29 - Sep 30
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A garden with a variety of flowers and trees at dusk.

3. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (161 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
$215 nightly
The price is $241
Sep 29 - Sep 30
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

4. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$186 nightly
The price is $209
Sep 29 - Sep 30
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A mountainous landscape with dense green forests and a clear sky.

5. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (333 reviews)
"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."
United States
Virginia
$209 nightly
The price is $234
Sep 29 - Sep 30
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A two-story house with a stone foundation, a large front porch, and a chimney.

6. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (123 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$234 nightly
The price is $263
Sep 29 - Sep 30
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

7. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (43 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$264 nightly
The price is $296
Sep 29 - Sep 30
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A two-story wooden cabin with a wooden deck and a small porch.

8. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Enjoyed our stay."
United States
Alice W.
$219 nightly
The price is $246
Sep 29 - Sep 30
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

9. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
$229 nightly
The price is $257
Sep 29 - Sep 30
Total with taxes and fees
Mountain View Vista
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

10. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (37 reviews)
"Great stay for my family!"
United States
Joel M.
$219 nightly
The price is $246
Sep 29 - Sep 30
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

11. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (48 reviews)
"Wonderful stay, wonderful place!! The view, the fireplace, well appointed, comfortable bed, comfortable furniture, very clean...will definitely stay again! Thank you!!"
United States
Art P.
$249 nightly
The price is $280
Sep 29 - Sep 30
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

12. Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
$270 nightly
The price is $272
Sep 29 - Sep 30
Total with taxes and fees
Mountain Retreat in Wintergreen!
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

13. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
$229 nightly
The price is $257
Sep 29 - Sep 30
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
A dining area with a wooden table, chairs, and a view of the kitchen.

14. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails

Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Wintergreen Resort
10.0 out of 10, Exceptional, (5 reviews)
$278 nightly
The price is $313
Oct 12 - Oct 13
Total with taxes and fees
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
A rustic building with stone pillars, wooden beams, and a covered entrance.

15. Blue Ridge Views, Dog Friendly, 2 Fireplaces

Blue Ridge Views, Dog Friendly, 2 Fireplaces
Roseland
10.0 out of 10, Exceptional, (76 reviews)
"The house was perfect in location and comfort. My husband and I along with our three daughters felt right at home and loved the amazing views. The owners were very attentive and responsive. "
United States
Anonymous traveler
$346 nightly
The price is $387
Sep 29 - Sep 30
Total with taxes and fees
Blue Ridge Views, Dog Friendly, 2 Fireplaces
A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a granite countertop.

16. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (15 reviews)
"The condo was beautiful and clean and worked perfectly for our group."
United States
Eric W.
$275 nightly
The price is $309
Sep 29 - Sep 30
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
A house with a covered porch, two Adirondack chairs, and a welcome mat.

17. Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (5 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
$270 nightly
The price is $272
Oct 12 - Oct 13
Total with taxes and fees
Cozy Lux Condo at Wintergreen Resort
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

18. Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
United States
Sarah L.
$276 nightly
The price is $310
Sep 30 - Oct 1
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

19. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
$305 nightly
The price is $343
Sep 29 - Sep 30
Total with taxes and fees
Firefly on The Ridge
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

20. Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Views from the porch are beautiful!Essentials ar all there Well thought out for a rentalHope to be back for another anniversary"
United States
rodney f.
$266 nightly
The price is $299
Sep 29 - Sep 30
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waynesboro Hotel Reviews

Grey Pine Lodge

Grey Pine Lodge

10/10 Excellent
"This location was very clean. The only things that we had an issue with was the room number was not on my itinerary so I had to call customer service to receive that info and also the supply room where you can self serve yourself to any items you wanted to buy the Cody they gave me was wrong and I couldn’t access, but other then those two things I will book again! Highly recommended."
Melanie 1-night trip
Posted less than an hour ago
Grey Pine Lodge

Find out more about Waynesboro

Waynesboro Condo Rentals information

Number of reviews
1,128
Accommodation
434 Condo Rentals
Lowest Price
$189
Highest Price
$387

Frequently asked questions

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Expedia can help you track down cheap condos in Waynesboro. To discover a terrific stay in a few quick clicks, use the filter tool to refine your search results by amenities, star rating and budget.
What is there to do in Waynesboro near my condo?
You'll find plenty of awesome things to sink your teeth into in Waynesboro. Check out leading attractions like Wayne Theatre, Basic City Beer Co. and P. Buckley Moss Gallery. Hermitage Hill Farm & Stables, Rockfish Gap Entrance Shenandoah and Zeus Digital Theater are also on many to-do lists.

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